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2000

Taylor Momsen

November 17

'Who' Debut

Momsen lands the kid role of a lifetime as little Cindy Lou Who in the live action remake of How the Grinch Stole Christmas with Jim Carrey. Momsen's performance charms audiences and earns her a Young Artist Award nomination. She follows Grinch with family flicks Spy Kids 2 and Hansel & Gretel with Dakota Fanning.

2007

Taylor Momsen

May

Going Indie

At 14, Momsen lands a supporting role in director Gus Van Sant's dark arthouse flick Paranoid Park, portraying the lustful girlfriend of a depressed skater suspected of murder. The risqué role, which includes a sex scene, is a departure from Momsen's squeaky clean image. "It's a totally different experience than anything I've ever done," Momsen tells Nylon magazine.

Taylor Momsen

September 19

Gossip's 'It' Girl

Momsen's turn as Jenny Humphrey on the CW's Gossip Girl makes her a household name. As the innocent rival of Upper East Side Queen Bee Blair Waldorf (Leighton Meester), "Little J" becomes a fan favorite. "I have two different modes: I have my on-set mode, and then I have...my Taylor mode," Momsen tells The New York Observer. "And when I'm in my Taylor mode, I forget that people still see me as Jenny. It takes a minute." The breakout hit costars Penn Badgley, Blake Lively, Chace Crawford and Ed Westwick.

2008

Taylor Momsen

April 28

Gossip Girl Covers New York

The cast of Gossip Girl strips down for New York magazine, which calls the teen soap "the most awesomely awesome show ever." That week, the entire cast also lands on PEOPLE's Most Beautiful List. "[She's] pretty much perfect," Chace Crawford tells PEOPLE of his young costar.

Taylor Momsen

June

Taylor Goes Edgy

The leggy blonde signs with IMG modeling agency and poses for an avant-garde spread for French magazine Crash. "I love high fashion," Momsen tells Blackbook. "It's been such a big part of my life, models and fashion, so it's really exciting to enter that world. It's a whole different ballgame." Trading her cutesy curls for a punk rock shag, Momsen goes glam goth as she makes her rounds on the red carpet party circuits.

2009

Taylor Momsen

A 'Reckless' Pursuit

With her new look comes a new outspoken Momsen, who jumps center stage as lead singer and songwriter of the rock band, The Pretty Reckless."I know people were a little, um, taken aback," she says of her rock star persona. "But it wasn't me that changed – it was just that I decided to start being myself." The band, which performs on the Warped Tour, signs a record deal with Interscope.

2010

Taylor Momsen

August

New 'Material'

Momsen leaves Jenny Humphrey behind to front the ad campaign for Madonna's Material Girl fashion line. "For one, it’s Madonna so you know it’s gonna be cool and working with Madonna and Lola has been an unbelievable experience," the actress-turned-rocker says of being styled by the mother-daughter design team.

2011

Taylor Momsen

May

Goodbye, Girl

After five seasons on Gossip Girl, Momsen bids farewell to her acting career. Passionate about her band The Pretty Reckless, the actress focuses on music. "Anytime you have an opportunity to play music, whether it’s in the studio or on the road, it’s the best thing in the world," she tells ELLE.

Photo Credits

BIOGRAPHY (top to bottom): Everett; Everett; Giovanni Rufino/CW; courtesy New York Magazine; Sara Jaye Weiss/Startraks; Jason DeCrow/AP; Courtesy Iconix; Giovanni Rufino/CW

Edited by Julia Wang

Taylor Momsen

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